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Reidentification of Sex Pheromones of Tea Geometrid Ectropis Obliqua Prout (Lepidoptera: Geometridae)

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Reidentification of Sex Pheromones of Tea Geometrid Ectropis Obliqua Prout (Lepidoptera: Geometridae) Journal of Economic Entomology, 109(1), 2016, 167–175 doi: 10.1093/jee/tov282 Advance Access Publication Date: 21 October 2015 Ecology and Behavior Research article Reidentification of Sex Pheromones of Tea Geometrid Ectropis obliqua Prout (Lepidoptera: Geometridae) Yunqiu Yang,1 Longwa Zhang,2 Feng Guo,1,3 Yanhua Long,3 Yun Wang,1 and Xiaochun Wan1,4 1State Key Laboratory of Tea Plant Biology and Utilization, Anhui Agricultural University, Hefei 230036, China ([email protected]; [email protected]; [email protected]), 2Provincial Key Laboratory of Microbial Pest Control, Anhui Agricultural University, Hefei 230036, China ([email protected]), 3School of Life Science, Anhui Agricultural University, Hefei 230036, China (yyq_ly- [email protected]), and 4Corresponding author, e-mail: [email protected]. Received 26 March 2015; Accepted 2 September 2015 Downloaded from Abstract Tea geometrid Ectropis obliqua Prout (Lepidoptera: Geometridae) is an important defoliator of the tree crop Camellia sinensis L. in China. The sex pheromones of E. obliqua have not been identified, but have potential im- portance relative to the biological control of this predator. In this study, the female sex pheromones of E. obli- qua were identified and evaluated for use in the monitoring and mass trapping of this pest. The sex pheromone http://jee.oxfordjournals.org/ extracts were subjected to gas chromatography–electroantennographic detection and gas chromatography– mass spectrometry. The identified chemicals were synthesized and applied to wind-tunnel tests and field exper- iments. (Z,Z,Z )-3,6,9-octadecatriene and 6,7-epoxy-(Z,Z )-3,9-octadecadiene were determined to be the primary sex pheromones produced by the female E. obliqua; the latter elicits the strongest electroantennogram responses from male E. obliqua antennae. However, males did not respond to single components in the wind- tunnel tests. The results of a field-trapping experiment indicated that a 4:6 v/v blend of (Z,Z,Z )-3,6,9-octadeca- triene and 6,7-epoxy-(Z,Z )-3,9-octadecadiene was highly effective in attracting male moths. Key words Ectropis oblique Prout, sex pheromone, (Z,Z,Z )-3,6,9-octadecatriene, 6,7-epoxy-(Z,Z )-3,9-octadecadiene, Camellia by guest on March 21, 2016 sinensis L Tea geometrid Ectropis obliqua Prout (Lepidoptera: Geometridae 9-nonadecatriene as sex pheromones of E. obliqua (Li et al. 1988). Ennominae) is a major pest that infests thousands of hectares of tea Yao et al. (1991) deduced that (Z,Z,Z )-3,6,9-octadecatriene and plantations (Camellia sinensis L) in China annually. E. obliqua can 6,7-epoxy-(Z,Z )-3,9-octadecadiene were sex pheromones of this also be found in Japan, but it is not considered a serious pest in that pest through gas chromatography–mass spectrometry (GC-MS). country (Hu et al. 1994). Outbreak populations of this pest can com- These authors also reported that (Z,Z,Z )-3,6,9-docosatriene and pletely consume all the leaves on a tea bush, thereby limiting tea pro- (Z,Z,Z )-3,6,9-tetracosatriene exhibit a certain capability to duction in summer and autumn severely and affecting tea production attract(Yao et al. 1991). However, Yao et al. did not present the for the following year (Hazarika et al. 2009, Zhang et al. 2014). E. field attraction data and the statistical analyses or details about the obliqua is multivoltine and produces six to seven generations per year doses and dispensers used. (Yang et al. 2008). Recurring E. obliqua outbreaks can be controlled The sex pheromones of E. obliqua have not been accurately iden- with large doses of chemical pesticides; however, this practice leaves tified; therefore, the use of pheromones to monitor and control this pesticide residues on the tea that is shipped to the market and pollutes moth in tea orchards has been hampered. In the present work, we the environment (Hazarika et al. 2001, Ye et al. 2014). As such, non- examine the active compounds extracted from the female sex phero- insecticidal measures must urgently be developed to control E. obli- mone glands of E. obliqua, the sensory responses of male moths to qua; the utilization of sex pheromones to manipulate behavior is a synthetic compounds, and the behavioral responses of male moths promising alternative to pesticides (Hazarika et al. 2009). as per wind-tunnel and field bioassays. Attempts to identify the sex pheromones of E. obliqua were initi- ated more than 30 yr ago. Du (1978–1981) studied E. obliqua sex Materials and Methods pheromones and identified multiple potential components, but the chemical structures of these components were not reported (date Insects unpublished). Li et al. (1988) identified (Z,Z,Z )-3,6,9-octadeca- E. obliqua insects were obtained from Qian-Shan County (31.5 N, trienyl acetate, (Z,Z,Z )-3,6,9-octadecatriene, and (Z,Z,Z )-3,6, 116.3 E), Anhui Province, China. Approximately 10 generations of VC The Authors 2015. Published by Oxford University Press on behalf of Entomological Society of America. All rights reserved. For Permissions, please email: [email protected] 167 168 Journal of Economic Entomology, 2016, Vol. 109, No. 1 this moth were maintained in the laboratory. Fresh material was col- although we modified their process slightly (Fig. 1). We used methyl lected regularly from the field and introduced into the laboratory linolenate (“1”) instead of linolenic acid to react with LiAlH4 in culture to prevent degeneration, and the larvae were reared on tea THF to produce the corresponding 9,12,15-octadecatrien-1-ol leaves. Furthermore, both adults and larvae were maintained under (“2”). Alcohol reacted with 4-methylbenzene-1-sulfonyl chloride controlled conditions at 22 6 3C, 60–70% RH, and a photoperiod (TosCl) in DCM converted to tosylate (“3”); then, tosylate reacted of 14:10 (L:D) h. Scotophase and photophase were reversed from with LiAlH4 in ether. Once the solvent evaporated, the crude prod- the natural light cycle to permit scotophase observation during nor- uct was purified through chromatography (PE ¼ 100%) to obtain mal working hours. The pupae were sexed based on the morphology (Z,Z,Z )-3,6,9-octadecatriene (“4”). The purity of the produced of the eighth-tenth abdominal segments and were maintained in (Z,Z,Z )-3,6,9-octadecatriene was >98%. (Z,Z,Z )-3,6,9-octadeca- moist sand for eclosion. The adults were housed separately in 240- triene MS (EI. 70 eV): 248 (1) [Mþ], 192 (11), 135 (6), 108 (41), 95 ml plastic jars and fed with 10% honey solution soaked in cotton. (32) [C7H11þ], 67 (60) [C5H7þ], 79 (100) [C6H7þ], 55 (44) [C4H7þ], 41 (70). Female Calling (Z,Z,Z)-3,6,9-octadecatriene was converted to a mixture of the The diel rhythm of calling behavior was observed in 1- to 3-d-old three corresponding mono-epoxydienes through oxidation with m- virgin females (N ¼ 50) that were individually placed in plastic con- chloroperoxybenzoic acid in dichloromethane (Ando et al. 1993). tainers and housed under the artificial environment. Observations The crude product was separated with a reversed-phase column were conducted under red light (3 lux) at 1-h intervals during (SEPAX-GP18, Sepax Technologies, Inc., Newark, DE) and eluted scotophase. with 80% acetonitrile. A portion of the three regio-isomers was then separated into individual monoepoxides with silica gel (200–300 mesh; Sinopharm Chemical Reagent Beijing Co., Ltd.) and then Downloaded from Extraction of Sex Pheromones eluted with 50% benzene in hexane. The elution order was 6,7- Active sex pheromones were extracted from the glands of 1-day-old epoxide < 9,10-epoxide < 3,4-epoxide. The purity of the produced virgin females (N ¼ 20) 5 h after the scotophase began. Mating was 6,7-epoxy-(Z, Z)-3,9-octadecadiene was 95% with respect to the most frequently observed during this period. The terminal abdomi- other positional isomers. 6,7-epoxy-(Z,Z)-3,9-octadecadiene MS nal tip, including the pheromone gland, was excised from the virgin (EI. 70 eV): 264(1) [Mþ], 235(1) [C16H27Oþ], 181 (2), 195 (1) female moth. The tip was immersed in 10 ll of redistilled hexane for http://jee.oxfordjournals.org/ [C13H23Oþ], 111(13) [C7H11Oþ], 97 (18), 95 (25), 81 (40), 79 4–6 h at room temperature. Experimental procedures were per- (27), 67 (100), 55 (78), 41 (82). formed under red light (3 lux) to facilitate observation and to avoid disturbing the insects. Then, the tip was removed and the extracts merged for either gas chromatography–electroantennogram (GC- Electrophysiology EAG) or GC-MS analyses without purification. EAG was conducted with an EAG apparatus (Syntech Co., the Netherlands) to test the electrophysiological activity of male E. obli- GC-EAG and GC-MS Analyses qua antennae in response to different doses of (Z, Z, Z)-3,6,9-octa- decatriene and 6,7-epoxy-(Z, Z )-3,9-octadecadiene. These antennae The EAG activity of the natural E. obliqua pheromone components by guest on March 21, 2016 was determined using a gas chromatograph equipped with an elec- were prepared for GC-EAD by exposure to 4 ml/s of humidified and troantennographic detector (EAD; Struble and Arn 1984). An charcoal-filtered air through a 35-cm-long glass tube (inner diame- Agilent 7890 gas chromatograph was equipped with an INNOWAX ter, 8 mm; outer diameter, 10 mm). Approximately 3-mm holes were capillary column (60 m by 0.35 mm i.d. by 0.25 lm, J&W Scientific bored into the glass tube to facilitate the insertion of a Pasteur pip- Palo Alto, CA, USA). The column temperature was programmed at ette and to administer the pheromone test stimuli.
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